Yellowish-brown vat-dyes.



ITED $TATE PATENT @FFEQE.

WILHELM BAUER AND ALFRED PIERRE,

OF OPLADEN, NEARCOLOGNE. GERMANY,

ASSIGNORS TO SYNTHETIC PATENTS CO.. INC.. OF NEW YORK, N. Y., A CORPORA- TION OF NEW YORK.

YELLOWISH-BROWN VAT DYES.

No Drawing.

CO \halogen I halogen l l NOQ CH? The new dyes are in a dry state dark crystals with '1 metallic luster which are soluble in concentrated sulfuric acid gener- They yield with hydrosulfite and caustic soda lye yellow vats dyeing cotton after exposure to air yellowish-brown shades fast to, chlorin and .'to light.

In order to illustrate the new process more fully the following example is given. the parts being by weight:-Q20 parts of 5.7- dichloroisatin and 262 parts of G-nitro-diacetylindoxyl are dissolved in 2000 parts of hot glacial acetic acid, and the solution is heated on the water-bath during 2 hours with 100 parts of concentrated hydrochloric acid. The dyestufi' which has separatedis .tiltered off after cooling, washed and dried.

It has most probably the following formula:

and crystallizes in violet needles having a metallic luster which-are soluble in concentrated sulfuric acid with a bluish-violet coloration: dyeing cotton from the hydrosullite vat in pure yellowish-brown shades fast to chlorin, washing and light. In the hydrosultite vat the nitro-coinptiind is converted into the amino-compound. The latter can be obtained in the following way: 20 parts of the nitro-conipound are reduced with 50 parts of sodium hydrosulfite and 100 parts of caustic soda lye 30 B. and 3000 parts Specification of Letters Patent.

Patented May 314, 1918.

Application filed March 23. 1915. Serial No. 16,418.

\Ve have found that new and valuable vatdyestufl's can be obtained by condensing inoXyls or their acidylized derivatives, which are substituted in position (5 by nitro or amino group with halogenated isatins. The reaction proceeds most probably 6. g. in accordance with the following equation:

I halogen of hot water. The amino-product is isolated by blowing air into the solution. 1t is filtered off washed and dried. It is a. dark brown powder. insoluble in the usual or-- ganic solvents soluble in concentrated sulfuric acid with a reddish-violet coloration.

The said coloring matters can, if desired, be halogenated, the halogenated products producing dyeings' of generally the same shade being faster than those obtained from the non halogenated products. For this purpose 1;. 5 20 parts of the finely powdered anlino-compound are suspended in 200 parts of nitrobenzene and to the mixture which has to be stirred 20 parts of brot' tin are added. while stirring isicontinued tie mixture. is heated in the interval of 3 hours to 150 C. and kept at this temperature during 3 hours. After cooling the product having most probably the formula:

boring most probably the following general R includes oxygen and hydrogen; ll, stands for :1 benzene nucleus which contains halogen; l? for u benzene nucleus which may contain halogen and which, contains in posi tion 6 the group" sultitc and caustic soda lye vats dyeing cotton yellowish-brown shades remarkable for their fustncss to chlorin and to light. substantially as described.

Q. The new products being vat dyestutls having most probably the following general formula 1, V CO C---TF) .LJ illJ ;0 ill, (//F \NH/ \NH/ h -l being s group containing only one nitrogen atom wherein R stands for oxy gen or hydrogen; R, stands for abenzene nucleus which contains halogen; R for u benzene nucleus which contain halogen and which contains in position 6 the group ,n N{\R:

which dyes are in 1*. dry state (lurk crystals with a metallic luster soluble in hot concentrated sulfuric acid generally with u Yl0- let coloration; and which yield with hydro sulfitc. mid caustic soda lye rats dyeing eotton yellowish-brcnn shades reinzirkable for their fastness to chlorin and Lo-light, sul) stz'zntiully as desc "bed. i

3. The new products being vet dyestuffs hzi'lng most probably the following atomic wherein ll, stands for a benzene nucleus which contains halogen; which dyes are in :1 dry stutc durlc crystals with n metallic luster soluble in hot concentrated sulfuric acid generally with a violet coloration; and which yield with hydrosuliitc and caustic soda lyevats dyeing cotton yelltm'isluhrown shades remarkable for their tustness to chlorin and to light. substantially as dcscribed.

l. The new products being rut dy'cstult's having most probably the following general formula:

1 ----c0 c--- o, 11 (l0 1 K y O being 21 vat dye derivable from 5.7-dichloroisatin and tinminoindoxyl, which is in a dry state a dark brown crystalline powder [11. s. [L. sfl 

